


12 Rounds

by Destiel_Cockles



Series: Wincest Drabbles & Ficlets insprired by pics/gifs [14]
Category: Supernatural
Genre: Anal Fingering, Anal Sex, Bets & Wagers, Body Part Kinks, Bottom Sam, Cock Rings, Dean is a Tease, Dirty Talk, Explicit Sexual Content, Inspired by GIFs, Large Cock, M/M, Masturbation, Mutual Masturbation, Nipple Play, Porn, Porn With Plot, Prank Wars, Sex, Sex Toys, Shameless Smut, Size Kink, Smut, Teasing, Top Dean, Top Dean Winchester/Bottom Sam Winchester, Wincest - Freeform, contains suggestive/nsfw gifs
Language: English
Status: In-Progress
Published: 2015-06-21
Updated: 2015-06-21
Packaged: 2018-04-05 12:37:43
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 6,805
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4180140
Author URL: https://archiveofourown.org/users/Destiel_Cockles/pseuds/Destiel_Cockles
Summary: <blockquote class="userstuff">
              <p>It started like every other war between them starts. Dean was bored, drunk and horny. That could either be a really good combination for Sam or really bad. Good because it meant they would be having hot passionate sex for the rest of the night, bad because if Dean was in the mood to mess around with Sam, which he so often was, he would turn it into a kinky prank war.</p>
            </blockquote>





	12 Rounds

 

 

It started like every other war between them starts. Dean was bored, drunk and horny. That could either be a really good combination for Sam or really bad. Good because it meant they would be having hot passionate sex for the rest of the night, bad because if Dean was in the mood to mess around with Sam, which he so often was, he would turn it into a kinky prank war.

“Hey Sammy,” Dean slurred.

Sam looked up from his laptop, he could see Dean’s eyes were pupil blown and when his eyes drifted down to his jeans he could see he was clearly aroused. Sam hoped Dean was too horny to play around because the only thing Dean liked better than having sex was teasing Sam until he was so horny he was begging for it.

Sam sucked in a breath and closed his laptop. “Yeah?”

“C’mere.”

Dean patted the couch and shifted, he was sitting with his legs splayed wide open, making it even more obvious that he was horny. Sam got up and sat down next to his brother. Dean leaned in like he was going to kiss him but only barely grazed his lips across Sam’s then pulled back. Every time Dean opened his mouth Sam could practically taste the whiskey, he could probably get drunk just by kissing him. Dean was smashed and Sam knew that he was up to something.

“How ‘bout we play a little game?”

“How about just for once we have sex like normal people and not do all kinds of crazy things?”

Dean chuckled and picked up a bottle of whiskey then took a long slow drink, finishing it off. He ran his hand down the front of his jeans, making a show of adjusting his big thick cock that was straining against the denim. When Dean shifted his jeans slid lower, almost past his hipbones and Sam realized he wasn’t wearing any underwear. The thought immediately made him so hard so fast he almost blacked out.

“First of all…we’re not normal.” Dean grinned and slid his tongue across his lips then continued. “Besides, I thought you loved having hot kinky sex.”

“I do…I just don’t want you torturing me until I can barely stand it.”

Dean leaned over to kiss Sam, his jeans dipping even lower. Sam sucked in a breath and closed his eyes. When he opened them, Dean was inches from his face.

“Thought you loved foreplay?” Dean asked as he kissed Sam heatedly on the lips then ran his hand down Sam’s muscular chest. Dean pulled Sam closer and Sam knew he was screwed. Dean could talk him into anything when he was kissing him with those incredible lips, talking in his low sexy voice and touching him.

Sam moaned softly as Dean sucked down on his neck while his hand traveled down the front of Sam’s jeans. His finger teased over his throbbing erection as Dean’s tongue slid up behind Sam’s ear. Dean exhaled, sending a shiver up Sam’s spine.

“C’mon Sammy, let’s have a little fun before I fuck that tight sweet ass. You know it’s even better when you’re on the brink of insanity then finally feel my big thick cock sink deep inside of you.”     

Sam sighed and nodded. Dean kissed Sam several times then pulled back. “Okay, so basically whoever breaks first loses. Winner gets anything they want.”

“What do you mean breaks?”

“You know, horny enough to beg the other person to have sex.”

Sam knew there was no way in hell he could win a bet like this. Dean was pure sex on bowlegs. Everything about Dean turned Sam on, his body, his voice, his huge cock, and then there was the fact that he was the dirtiest dirty talker ever. He made porn seem like Saturday morning cartoons, and Sam would never be able to compete with that. But the biggest advantage Dean had over Sam was he was practically a sex god. Dean said he was a sex god all the time and although Sam would never come out and admit it to his brother because his ego about his sexuality was insufferable enough, deep down Sam thought it was true. He had the biggest dick Sam had ever seen and he knew how to use it better than anyone and Sam knew everyone who had sex with Dean before him felt the same way because he heard about it his entire life. Then there was the fact that every kiss and touch was pure ecstasy, Dean always drove him insanely horny and if they had a bet going Dean would turn it up so much Sam knew he would never win but the more he thought about it, he was not really losing because they were going to end up having amazing sex. Since Dean was much kinkier in a way it would be better if he won. Sam wished his brother would just have sex with him rather than playing games but Sam secretly kind of liked Dean’s immature way of doing things because it kept things interesting.

“Fine…but there has to be rules and it has to be fair.”

Dean smiled seductively at Sam. “Of course.”

Sam sighed. He knew Dean was playing him because he was trying to act innocent but Sam knew his brother well enough to know he already had the entire thing planned out. Dean had to be planning something pretty sexual because he was making a point to go to the trouble of making a bet which made Sam even hornier because it meant it would be even kinkier than normal.

 “So…what were you thinking?”

“Like I said, gotta make the other person horny enough to give in and beg to have sex. There is one catch…”

Sam knew there would be a catch. He took a deep breath and was almost afraid to ask.  “What’s the catch?”

“You can’t touch the other person. If you do, you automatically lose.”

Sam considered it for a moment, it sounded easy enough because he knew Dean, he was the most impatient person on the planet but when it came to sex, Dean didn’t like fucking around—he liked to fuck. Sure he loved teasing Sam but Dean always caved once he got horny and when Dean got horny he got grabby so he would have a pretty hard time especially since he was drunk.

“Fine…you’ll be begging me to have sex here in a few minutes.”

Dean chuckled as he slid his hand over the huge bulge in his jeans. “Bull. I’ll have you on your knees begging me. While you’re down there you can suck my dick.”

“Your dick looks pretty hard, you’re horny as fuck and you’ll be pouncing on me any minute.”

“As much as I want to…you know I won’t. When have I ever lost a bet?”

Sam hadn’t thought of that. Dean was even more competitive than he was impatient. He had to win, no matter what. That meant it could be days before they had sex. They had never gone more than a few hours, having sex at least five times a day sometimes double that. Even if Sam wanted to give in and let Dean win he couldn’t because Dean would never let him live it down so he had to make it at least a few hours before he gave in.

“You honestly think you can go a day without sex? I know I can’t.”

Dean seemed to be thinking it over. He knew Sam was right, there was no way in hell either of them could go that long but all he really had to do was make Sam cave first and Sam had just admitted he couldn’t go without sex. Dean knew it would he harder for Sam to win if they couldn’t touch because Dean had the advantage of talking dirty over Sam, he knew it got to him so all he’d have to do is lay it on extra thick and they would most likely be fucking within the hour.

“Fine, you think I can’t go an entire day without sex, we’ll see.”

“Fine.”

Sam knew his was a horrible idea, Dean was going to torture him to no end but there was no way in hell he could back out now so he decided to just go along with it because Dean was drunk as hell and that made him hornier than hell. Sam reasoned that Dean was closer to his breaking point already because it looked like his jeans were about to burst open from his erection straining against them.

Dean stuck his hand out and Sam rolled his eyes. He shook Dean’s hand and suddenly had a realization as Dean smiled seductively at him. Dean was always doing things that drive him insane without ever touching him, in fact now that he really thought about it Dean got him to the brink of insanity before they started messing around. Not just because he was gorgeous and sexy, but because he always did things that drove Sam over the edge, like how he eyefucked the shit out of him and his deep sexy voice, then there was that dirty mind of his, he was so unpredictable and would do anything so Sam knew he was literally screwed.

Sam glanced over at his brother. He had moved to the other end of the couch and had his legs splayed wide open. Dean had his jeans open and his hand inside, slowly stroking himself. Sam sucked in a breath, he tried looking away but his eyes were drawn to Dean’s arm slowly moving as his hand twisted up and down his dick.

Dean saw Sam’s eyes on him so he stopped long enough to take his shirt off then slid his hand back inside his jeans. He was horny as hell so he had to get Sam to crack. He was pretty confident he could get Sam to beg him to fuck because once Sam got horny he normally could not wait to have sex. But they were both competitive, neither of them wanted to lose a bet and even though Dean had never lost a bet or prank war they had never really had a bet like this and although he was pretty sure he would win, he really was not in any condition to wait because even though he was getting to Sam it was making Dean even hornier to be teasing Sam especially because he could tell Sam wanted to have sex just as bad as he did.

Dean pushed his jeans down slightly, just enough that Sam could see the base of his cock. He saw Sam suck in a breath as he leaned over the arm of the couch and reached for the remote which caused his jeans to dip down even lower. He turned the TV on and grinned. Casa Erotica 17 was on, one of his favorites. He cranked the volume then looked over at his brother and his grin widened. Sam already looked horny as hell so Dean figured if he started jerking off Sam would eventually get to the point he couldn’t take it and even if he didn’t beg Dean to have sex he would touch him and automatically lose.

Dean slid his hand back in his jeans, sucking in a breath as his fingers brushed against the head of his cock. He started jerking his fist up and down then moaned as he looked at Sam. Dean paused and sucked in a breath, closing his eyes.

"Gonna make me do this myself?"

When Sam didn't answer him, Dean started twisting his wrist up and down faster, trying to get into it more. Sam rubbed the front of his jeans, they were so tight they felt like they were two sizes too small. Dean’s free hand slid up his abs and chest. He slowly started to run his fingers over his nipple and could see Sam biting his lip as he turned his head and pretended to watch the TV but Dean knew Sam didn’t really get into porn so he had to get his attention back on him.

Dean shoved his jeans down his thighs then decided to just take them off. He shifted so he was facing Sam and started pumping his hand up and down his cock. He knew it got to Sam when he made noise or talked dirty so he decided to do both.

“Mm _shit_ …” Dean bit down on his lip and thrust into his fist. “Want some of this big fat dick, Sammy?” Dean glanced up at Sam and saw him shift so he groaned loudly and closed his eyes, getting even more into it. “Damn, I wish I was fucking your tight ass right about now. I’d be fucking you so…” Dean thrust quicker into his fist and groaned, “So damn hard, fuck you so hard you’ll feel me for an entire month.”

Dean started grunting as he pumped his fist quicker. He was getting to Sam but he had to turn it up more. Dean sucked on his fingers then spread his legs apart, hooking a leg over the back of the couch so that Sam had an excellent view of everything. Sam felt his cock twitch hard in his jeans as he stared at his brother’s fully exposed gorgeous muscular body.

Dean slid a finger down his perineum, pausing to rub it then moaning as he pressed down harder. His finger continued to trail down over his rim, while he stared straight into Sam’s eyes he slowly worked a finger inside. Dean quickly worked another finger in, grunting as he pounded down on them and thrust into his fist making sure to make as many hot noises as he could.

“Which would you rather feel?” Dean paused and scissored his fingers, groaning as he continued, “My big cock filling you up, or be in my tight sweet ass?”

Sam’s breathing was quickening and Dean could see him sweating. His jeans were growing tighter by the second and his pupils were blown so big Dean could see them from across the couch. It had been awhile since he had to jerk off, it wasn’t nearly as satisfying as it used to be, nothing was except having sex with his brother and he knew Sam felt the same way so if he could just get him to start doing it and realize it sucked compared to having sex then he was sure Sam would break.

“Bet you’d love to feel my lips wrapped around your cock right about now, huh?”

Dean watched Sam’s eyes flicker down to his lips so he slowly slid his tongue across them then bit down on them as he eased a third finger in. He said his brother’s name in a breathy moan and saw Sam’s fist grip the edge of the couch so tight his knuckles were white.

“Mm yeah…imagine my thick plump lips around you, feeling my hot wet mouth swallowing you down…” Dean paused and moaned. There was so much precome sweating out of his cock it was making an obscenely hot noise as his fist pumped up and down. He could see Sam’s eyes darting back and forth from his lips to his hand jerking up and down then to his fingers. Dean pushed down on his fingers harder, pausing as he hit his prostate hard. _“Fuck!_ Damn, wish it was your dick hittin’ my sweet spot…bet you wish you were in my tight heat right now…. _so_ fucking tight…ready too. You could just thrust right in…”

Dean eased a finger out and spread the remaining two. “See, nice and ready for you. C’mon Sammy, you wanna feel just how tight I am, don’t you? You know it’s been a couple days since you did me…always wanting my dick and _shit_ , I’m happy to give it to you as much as you want but I know you’re practically salivating over there. You wanna slide that tongue in me, taste me then you wanna fuck me, don’t you? Yeah, I know you do I can see it. Why don’t you take those jeans off?”

Sam shifted uncomfortably, Dean knew how to get to him and he was just about at his breaking point. He desperately wanted to have sex with Dean and Dean knew it. Looking at him was torture but he couldn’t look away and even if he wanted to get up he couldn’t because it felt like he was stuck to the couch.  Dean was like a siren, captivating him and Sam was just about to succumb to him when he remembered it had only been about five minutes since they made the bet, that would be a record for Sam losing and he would never live it down. He was dying to take his jeans off, the denim was so tight around his erection he could barely stand it and he knew if he didn’t take them off and continued to watch his brother and listen to him that he’d just cream his pants anyway so he might as well get a little stimulation.

Dean smirked when Sam unzipped his jeans and barely had them pushed down his thighs as he made a tight fist around his cock. “Feels good huh? You know what would feel even better? My big fat cock pounding into your tight little ass.”

Sam closed his eyes, he had been fiending for Dean to fuck him before any of this even started now he was desperate. He wondered why he let his brother talk him into such stupid idiotic games. He should just tell him how ridiculous this was and then they could be having sex. Sam opened his mouth and looked at his brother just as Dean slid his pinky in under his other fingers. Watching Dean finger himself while he jerked off was one of the hottest things Sam had ever seen. He moaned and softly said his brother’s name.

“Am I getting to you? Ready to give in? I’ll even give you a freebie before I do whatever I want when I win. You can fuck me first because trust me when I’m done with you…you’re gonna be in an ecstasy coma.”

Sam’s fist moved up and down faster, Dean was surprised his brother wasn’t giving in yet. He had been planning on doing some kinky things with Sam all week but wasn’t sure how to get him on board with it and that’s when he came up with the idea for the bet. Just as he predicted, his brother was struggling but still holding out because even though Sam always lost bets he did last longer each time. But Dean knew when it came to sex with him, Sam would never make it more than a day so in preparation Dean had bought a few things, some for when he won and others to help him win.

Dean eased his fingers out and sat up. Sam watched as Dean walked over to his duffel bag and pulled out some lube. He saw him get a bag and wondered what he was up to. Dean returned to his spot, sitting towards Sam and opened the lube, pouring a ridiculous amount in his hand.

“Let’s see how long you can last…I say in the next five minutes you’re gonna be jumping over here and holding me down.”

“Please, I can make it a hell of a lot longer than five minutes.”

“Might want to just go ahead and take the rest of your clothes off now.”

Sam wasn’t sure what Dean was up to but it was uncomfortable to have his jeans half on so he kicked them off. Dean motioned to his shirt and grinned.

“Wouldn’t want to get jizz on your shirt, better take it off.”

Sam hesitated, he didn’t have too many clean shirts left and didn’t feel like going to do laundry but he didn’t want Dean to think he was giving in. Dean seemed to be waiting so Sam rolled his eyes and gave in.

“Well I knew you would never make it more than an hour…but I also knew I didn’t want to wait more than an hour…”

Dean pulled a vibrating dildo out of the bag, smiling when he saw all of the color drain from his brother’s face. His hand gripped his dick harder and Dean could tell he was dying to watch him play with it.

“If you want to give in right now, I’ll let you shove this in me…or hell, you can shove it up your own ass. Even though it isn’t as big as me, it’ll still feel good as fuck.”

Dean turned it on, sliding his tongue across his lips as Sam bit down on his lips and groaned as he thrust into his fist. Sam had always wanted to watch his brother play with sex toys and he had wanted to use them on him even more but Dean always said they didn’t need them and wasn’t into them. Sam was sure Dean was just doing this to get to him, he had obviously planned this out but Sam no longer cared about losing he wanted to watch Dean play with it then he wanted to drive Dean over the edge with it.

“Oh, and I bought a few other things…for after I win.”

“Wh-what did…what did you get?”

Dean smiled seductively at his brother as he slowly teased the dildo over his rim. He noticed Sam didn’t object to Dean saying he was going to win because all he cared about was the sex toys just like Dean knew he would. “Mm shit…guess you’ll find out if…I mean _when_ I win…”

Dean trailed off and slowly slid the toy halfway in then eased it out. Since Sam didn’t object again Dean knew he had him so now his mission was to drive his brother completely insane.

“Do you want to watch me do this?”

“Y-yes,” Sam responded in a low strained voice.

“You horny?”

“Fuck yes.”

“Tell me what you want me to do with it.”

Sam’s mouth suddenly went completely dry. He picked up a bottle of tequila sitting on the table and took a few sips. “Fuck yourself with it.”

“You gonna play with it for me later? Only way I do it is if I get to watch you fuck yourself with it because I know you’ve been dying to do that, haven’t you, Sammy?”

Sam nodded as Dean slowly slid the entire dildo in and out, gradually picking up speed. Sam was watching him intently, he had shifted closer and his eyes were fixated on watching his brother play with the toy. His hand moved up and down his cock in rhythm with Dean’s.

“T-turn it on.”

Dean bit down on his lip and turned it on, throwing his head back and letting out a string of moans and curses, causing Sam to start thrusting harder into his fist. Sam could see Dean’s body shuttering as he pushed down on it hard then paused, it was obviously hitting his sweet spot and the hot porn quality noises that were flying out of his brother’s mouth were driving Sam completely insane.

Dean teased it up near his balls then slowly pulled it in and out, gradually increasing his speed until he was thrusting it in fast. He bit down on his lip and started grunting and moaning Sam’s name. Sam couldn’t take it anymore. He didn’t care if he was losing a bet this was the hottest damn thing he had ever seen in his life and he wanted to shove that damn dildo into his brother even more than he wanted to do it to himself. Sam jumped up and grabbed the toy out of Dean’s hand. Dean licked his lips and smirked.

“You giving up already?”

Sam’s eyes were dark, his face flushed. He nodded and Dean’s grin widened.

“Yeah? Damn, that was a hell of a lot easier than I thought…what made you cave so damn fast?”

“You know.”

“Yeah…but I wanna hear you say it.”

“This damn thing…watching you fuck yourself with it is so goddamn hot but I'm dying to fuck you with it even more.”

Sam turned it on and teased it across Dean’s rim, practically drooling as Dean pushed down on it hard and groaned when it started vibrating against his prostate. Sam turned it up all the way and held it so it was vibrating against Dean’s sweet spot. Sam ran his hand up and down his aching erection as Dean’s back arched up and he yelled Sam’s name between clenched teeth. Sam reached up and tried circling his fingers around his brother’s dick but Dean slapped his hand away. When Sam looked up at him Dean grinned.

“I won…and I’ll let you…” Dean paused and groaned as Sam slid the dildo out then shoved it back in hard. “Son of a fucking _bitch_ …turn that damn thing off for a second before I come all over your face.”

“I want you to.”

Dean chuckled and slid his tongue across his lips. “I’ll let you but first…gotta do what I want the rest of the night.”

“What? You didn’t say all night.”

“Didn’t I?”

Sam sighed, he knew better than to argue with Dean. He also knew Dean had more toys and would most likely use them on him until he caved so Sam asked him what he had to do.

“Play with yourself using it first…then you can do whatever the hell you want with it to me…”

“What’s the catch?”

“No catch…just wanna watch you fuck yourself on it since you’ve been begging me to get this stupid shit.”

“Don’t act like you didn’t love it a few seconds ago,” Sam grinned as he turned it on and ran it up Dean’s balls and slowly across his cock.

“Yeah, whatever. But then after you get to play, we fuck…”

“Yeah?”

Dean smirked. “Not telling you anymore…the rest depends on you.”

“What do you mean?”

Dean pushed Sam back and kissed him then stood up and grabbed his wrist, dragging Sam over to their bed. He shoved Sam down and grabbed a pillow and lay on the opposite end, facing his brother.

“Put on a good show for me, really get into it.”

Dean leaned forward and reached under the pillow, grabbing the lube. He grabbed his brother’s hand and poured most of the bottle out and smiled seductively at him.

“Make sure you don’t hold back. I wanna hear how much you love fucking yourself on this dildo.”

Sam poked his middle finger against his puckered holed, sliding it in then quickly working another finger in right after. Dean chuckled under his breath as Sam scissored his fingers then sucked in a breath as he jammed in a third.

“Holy shit, you’re dying to get that thing in you…slow down. Enjoy yourself it’s not a fucking race.”

Sam was in a bigger hurry to use it on Dean, but he wanted his brother’s cock in him even more because the dildo wasn’t as thick or long as Dean. He didn’t think it would turn him on so much to see his brother playing with the toy but it did and even though Dean didn’t come out and say it he seemed to really like it especially when Sam had it vibrating.

Dean cursed under his breath as he watched Sam slide the dildo in and started thrusting down as he pushed it in and out of himself. It was pretty damn hot, so hot he could probably get off just watching Sam play with it. He didn’t even realize he was pumping his hand up and down his cock until he felt it twitch hard in his hand when Sam said his name in a breathy moan.

“Fuck Sammy…you’re killing me.” Dean bit down on his lip and tightened his grip, thrusting into his fist a few more times then stopped before he came. “Turn that damn thing on…no wait, let me do it.”

Sam slowly eased the dildo out and handed it to Dean. He watched Dean’s grin widen as he quickly knelt up and shoved Sam’s legs apart. Dean bit down on his lips like he was thinking something over then he grabbed Sam’s thighs and pulled his legs over his shoulders. Just as Dean started teasing the tip of the dildo in he got off the bed.

Sam made an impatient noise. “Dean, what the fuck?”

“Calm down it’ll be worth it.”

Dean knelt back on the bed and leaned down and kissed Sam. “Don’t freak out…”

Sam wondered what Dean was going to do as Dean started kissing him with more intensity. He felt Dean slide his lubed up hand up and down his cock then slid something cold over it. He pulled back and shoved Dean back.

“Do we really need cock rings? I mean we normally fuck all night no problem…and neither of us has ever had a problem lasting…”

“Yeah, but it’ll make this orgasm more intense and trust me you want this one to last longer.”

Dean put a cock ring on himself then tossed Sam a small remote. “I’ll even let you be in charge of them.”

“They vibrate too? Oh _shit!.”_ Sam groaned and held the button down. When he saw his brother bite down on his lip and groan he held it down for several seconds.

“Jesus, wait ‘til I get this damn thing in you.”

Dean teased the dildo in and out, barely sliding an inch or two in at a time. “I’m not gonna lie…it’s pretty hot to watch you play with this thing but I’m gonna be fucking you here in a second, and not with this damn thing.”

“You could um…”

“What?”

Sam blushed and looked down, shaking his head. “Nothing…just _please_ do it I’m so fucking horny and this damn ring is making me so hard I’m going to explode.”

Dean smirked and turned the vibration on. “Nah, it’ll delay your explosions.”

“Shut up.”

Dean slid the dildo in and started pumping it in and out when it suddenly hit him what Sam had almost said but stopped. “Wait…are you…oh _shit_ I had no idea you’d ever get _that_ kinky… _fuck.”_

“So you’ll do it?”

Dean started pumping the toy in harder, turning the vibration on when it was all the way inside and then holding it against Sam’s prostate. “You sure you wanna do that, I mean…dude, that might hurt and I don’t think I can get all the way in with this in you already I’m not exactly small you know.”

“I know…which is why I want you to fuck me then just inch it in a little underneath….”

Dean pulled the dildo out and looked at his brother. “You sure about that? I mean it would be right up there with like…fisting or something and we don’t…”

“You scared?”

“What? No, but I’m not the one getting stretched out and you can barely sit down when I’m done with you can you even imagine…it would be hot as fuck though…”

Dean slid three fingers in then slid his pinky in underneath. Sam bit down on his lip as Dean gradually stretched him out more. Sam groaned as Dean shoved his fingers in deeper, suddenly glad his brother thought of the rings because he would’ve probably come already. Dean barely slid his thumb in too then pulled back.

“Tell me if you change your mind though…I don’t wanna ruin your perfect tight ass.”

“If I’m still tight after you fucking me all these years I think it’ll be fine.”

Sam had a point and if it were anyone else Dean would have been doing it already. He nodded and teased the head of his cock into his brother. Sam glanced up at him when Dean thrust all the way in, he normally teased him relentlessly and although he had been playing games for nearly an hour getting him hyped up he never just thrust in all the way.

“Is it not tight enough now?”

“You’re still tight as fuck, quit worrying I was joking…” Dean paused and moaned as he thrust in harder. He leaned back and pulled Sam’s legs over his shoulders then rammed in and groaned. _“Fuck_ , I’m so goddamn hard right now…”

Sam nodded then it hit him. He totally forgot about the cock rings. As soon as Dean thrust into him he turned them on. Dean grunted and his eyes slammed shut as his teeth began worrying his lips. “Fuck Sammy! Oh _shit_ you should warn me before you do that…son of a fucking _bitch!”_

No way Sam was going to warm him, he loved his reaction. He shut them off even though the feeling of it against his cock and also feeling the one Dean was wearing when he was in him all the way tight against his ass was incredible because he wanted to wait until Dean got into it more.

“You want me to work that dildo in yet?”

“Not yet…want you to fuck me hard for a few minutes.”

Dean held onto Sam’s hips and started pulling him into his thrusts. Sam felt Dean make a tight fist around his dick and gasped. Dean was right, the ring had made him about ten times harder and it actually felt even more incredible. Dean was obviously thinking the same thing because he was pummeling into Sam, cursing and moaning each time he bottomed out.

“Dean! _Shit_ …” Sam felt a jolt of intense white hot pleasure surge through his entire body as Dean slammed into his prostate. He closed his eyes and felt Dean let go of him then he suddenly felt Dean sliding the dildo, on the highest vibration setting, up and down his over sensitized cock. “Holy shit! Feels like I’m having an orgasm… _fuck_.”

“Mm yeah you fucking love it don’t you? _Shit,_ you’re so fucking tight right now…goddamn.”

“Right, your dick feels so fucking hard and even bigger.”

Sam turned the vibration on the rings on and heard Dean choke out a moan as he started to pound into him harder. Sam’s back arched as he felt Dean plunge in hard and he paused, savoring his brother’s tight heat. Sam could feel the vibration of the cock ring on his brother against his rim. He yelled out Dean’s name and started shuddering. Dean circled his hips and slid the vibrator across the head of Sam’s dick.

“Dean! I-“

Sam’s voice cut out as Dean started pummeling into him with hard powerful thrusts. Dean shoved Sam’s thighs up as far as he could for several minutes then eased out. Sam opened his mouth to protest but Dean quickly responded, “Think that was good? Just wait ‘til I fuck you into the mattress.”

Dean got up and pulled Sam off of the bed. He spun around then pushed down on Sam’s back as he bent over. He held his brother open then thrust in as hard and fast as he could, quickly setting a brutal rhythm that had both of them moaning and grunting with pleasure, screaming out curses and each other’s names.

“Son of a fucking bitch…should’ve done this ages ago…”

“I kept telling you.”

“Shut up…” Dean paused and grabbed onto Sam’s hips, pulling him into every thrust. “You only said about dildos not rings or shit that vibrated…Think this is good? Just wait ‘til later.”

Sam sunk down further on the bed, groaning as Dean started inching the dildo in. “Do it Dean, _fuck.”_

“You sure?”

“Yes, just fucking do it!”

As soon as Dean had the dildo worked in he turned it on. Dean felt Sam clench down and groaned, the tightness of Sam around him and the movement of the dildo along with the vibration was almost too much.

“Turn the rings off... _fuck!”_

“Why? Doesn’t it feel good?”

“Hell yeah but I’m not gonna last much longer if-”

“I’m not either but we might as well leave it on so it’s that much better.”

Dean grunted a response, feeling much too incredible to attempt to form a coherent sentence. Sam got even tighter around Dean, his cock was so hard it was almost painful, he could feel come beading out and even though the last twenty minutes felt like an orgasm he could feel an even stronger one coming on. Dean reached down and started pumping his fist up and down Sam’s cock, thrusting in as he shoved the dildo in and out in rhythm with his thrusts.

Sam screamed out his brother’s name and a litany of hot porn quality noises then started coming, clamping down on Dean so hard it felt like he was milking the come out of him. Sam pushed the button when he felt Dean drop down over him, they were both shuddering with pleasure and struggling to breathe. Sam felt completely boneless and even though his brother was crushing him he could give a fuck less because he was currently feeling so much blissful ecstasy, just like Dean always promised when he fucked him, it felt like he was in an ecstasy coma.

Dean carefully pulled out then then managed to shift enough so he wasn’t crushing his brother then collapsed on the bed. After a few minutes Dean looked at Sam and smirked. “Now it’s time to have some real fun.”

Sam watched Dean as he climbed off the bed and got another bag. When Dean sat back down Sam tried grabbing it out of his hand but Dean held it out of his reach and smirked. He reached into the bag and pulled out a blindfold. Before Sam could protest, Dean had it over his eyes and grabbed his wrists in one hand while he reached under his pillow and took out a pair of handcuffs. He leaned in and brushed his lips against Sam’s pulling back when Sam tried kissing him.

“So…you liked that little bet, huh?”

Sam nodded and tried tugging on the handcuffs which Dean had tied to the bed post. Dean chuckled and kissed Sam, muttering against his lips as he continued kissing him.

“Relax, Sammy.”

As Dean continued to kiss Sam with more intensity Sam slowly stopped struggling. He felt Dean shift then start sucking down on his neck.

“If you’re good I’ll take the restraints off but first I gotta ask you something.”

“What?”

“How ‘bout we play the same game tomorrow…see who can last longer. Only this time, winner gets whatever they want for an entire _week_.”

Sam gulped. He knew he would never win but he was sure that Dean had plans and so far he loved where Dean was going with this. Sam slowly nodded as he answered his brother.

“Uh…I guess.”

Dean leaned up and kissed Sam, grinning. “Perfect…so just lay back and enjoy tonight because tomorrow I’m not gonna be so easy on you. Maybe you’ll even be able to resist me for an hour, since you know…today I had you in like, ten minutes.”

“Bull, it wasn’t that quick.” Sam chewed on his lip and thought for a minute. “You wouldn’t have won that quick if you hadn’t busted out the dildo…so tomorrow you can’t use it to get to me.”

Dean reached for the dildo and slowly slid it down Sam’s quickly hardening cock. When he turned it on Sam groaned and his back arched up in the air. “Yeah, because you know you’ll lose since you love watching me pound this thing up my ass almost as much as you love me pounding it up yours. Alright, tomorrow no gimmicks, just you and me and we’ll see how fast you fold.”

Sam didn’t need to see his brother to know he was grinning devilishly at him. He knew Dean already had a plan and Sam could hardly wait to see what he had in mind even though he would never admit it to Dean, Sam was actually sort of liking the thought of Dean driving him totally insane then being able to do anything he wanted then he might actually have to come up with a way to beat Dean because he had a few things he has always wanted to do with him too.

 

 

 

**Author's Note:**

> I decided to leave what Dean does to Sam for the next part...I have plenty of gifs for this so it will continue with a few more rounds


End file.
